Innovation

From chaos to clarity: inside one entrepreneur’s systems overhaul

Headshot of Susan Treiman
Sue Treiman January 7, 2025
A person with curly hair and glasses smiles as they present at a workshop, pointing at a whiteboard filled with colorful sticky notes. They wear a casual blue shirt.

When one of Jasmin Plouffe’s clients complained that her business processes were “unclear,” the entrepreneur reached out to a seasoned troubleshooter and fellow digital business owner for professional counsel. Her go-to resource was operations specialist Diane Lam, CEO of Diane Lam Co.

“I didn’t even hop on a discovery call,” says Plouffe, who runs a design and branding agency. “I just said, ‘I’m interested and ready to give you my credit card.”

Plouffe suspected that a total overhaul of her communications, marketing and project software could unscramble the communications snags that left her client feeling uninformed as the project neared completion.

“I wanted something that would organize all my work products for multiple clients and help them understand the process without adding to my workload,” says Plouffe.

Turns out, that’s exactly the kind of challenge Lam takes on.

Diane Lam sits on a sofa with a laptop resting in front of her. She gestures enthusiastically, as though on a video call.

The optimization queen

Before establishing her own company, Lam helped top financial executives set up, organize and run the technology infrastructure that supported their sales, marketing, client onboarding and offboarding, service delivery and administrative tasks. ‌

The experience familiarized her with countless technologies and applications. It also left her with a solid understanding of which approaches worked best to monitor essential record-keeping, billing and project operations. But doing all that work for a massive corporation just didn’t feel right.

Six years ago, she traded in the security of big business for the rough-and-tumble world of digital start-ups.

Today, Lam works with a predominantly female clientele made up of virtual coaches, consultants and creatives. Many of these new business owners rely on popular business management platforms–like Honeybook or ClickUp–without fully mastering the program’s capabilities and limitations. Not surprisingly, as their companies approach–and eventually surpass–$100,000 in annual revenue, their programs began to fray at the seams.

Often, it's because the owners didn’t fully understand the technology in the first place and may not have configured them appropriately.

“When digital entrepreneurs reach this point, they begin to have trouble managing all the work while maintaining their marketing and sales, “says Lam.

Digital troubleshooting

The jarring client feedback highlighted a growing concern: The increasing responsibilities of her business were becoming an ongoing battle.

Plouffe was having trouble keeping multiple clients updated about multiple projects. She struggled to manage the increasing hours she spent at work while also bringing in new business and completing everyday billing and office administration.

She had hoped the software she’d chosen would handle the bulk of her office responsibilities and allow time for the creative process.

Lam quizzed Plouffe about her concerns, goals, personal priorities and her technology infrastructure, including all the software and applications that touched her projects at every step of the production process.

Lam quickly detected a major problem. The Honeybook customer relationship management program Plouffe relied on for client updates was not configured for a high-touch service like hers. Without a way to consistently inform clients of the current stage of the project, they felt left out and confused.

“We needed to prepare clients to have a good experience with her, while better using her own time,” says Lam.

“Jasmin was going back and forth with clients saying, ‘now we need this, now we need that,’ rather than having an up-front way of communicating which documents and which materials she would need access to, and storing them in an accessible way,” explains Lam.

During in-depth work sessions, Lam and Plouffe reworked the start-to-finish production process for her branding project. They created a systematized way of establishing client expectations upfront, determining what materials would be needed throughout the process and then making it possible to collect, store and update those items on a site that would be available throughout the production cycle.

The result was a hybrid approach that harnessed what Honeybook does best–its standard templates. Some steps could be standardized across clients, including the general brochure information, “how we work” details, onboarding requirements, contract language, updates and invoicing.

In other cases, Plouffe enhanced the templates with client-specific extras tailored to their individual needs, including preparing a video walkthrough for some clients. The direct-to-client messages made her customers feel seen and involved in the process. A major step forward, even while the videos themselves could be brief and easily captured on a smart phone.

“We streamlined the process, made it faster and leveraged automation to wrap up many common steps into one package, laying out exactly how the the business would work with clients, ” says Lam.

They also leveraged the ClickUp application to house private, project-based sites where clients could track, view and approve the latest iteration and provide comments.

“It was very clear and streamlined for the client, showing exactly where the project was, when approvals would be needed and what the timing was,” says Lam.

The blueprint for change came with Lam’s continued coaching.

“I talked her through the technology set up, the different pieces that needed to be put in place and the way to structure those operations,” she adds

Signs of trouble

Like most clients, Plouffe had sensed that things were beginning to spin out of control well before anyone raised the red flag. ‌Also like many of her fellow digital entrepreneurs, Plouffe spent precious time trying to devise her solutions before engaging someone who could provide big-picture counsel.

That’s where Lam offered the kind of objective help that led to change. In Jasmin’s case, Lam could quickly see that the problem wasn’t with the particular software but how she was using it.

“I’ve seen similar issues throughout my almost 20 years doing operations optimization and that’s something a new entrepreneur may not have seen this or worked with a particular business model enough,” says Lam. “Entrepreneurs are great at what they do, but that doesn’t mean they excel at everything.”

Instead, she suggests finding a “done for you” pro who can complete the assignment quickly and accurately rather than attempting to devote many hours to cultivating a skill that may never again be needed.

Lam cautions digital entrepreneurs to pay close attention to early signs that trouble may be brewing. They include:

  • Trying to do everything: When “feeding the technology” steals time from other tasks, it's essential to reevaluate. The first indication can be seen in lagging sales and marketing efforts. “Most people can sense when they’re approaching or hitting capacity because they’re so busy doing all the work that they can’t plan ahead,” says Lam.
  • Putting big energy into small things: Struggling with tasks that fall outside an entrepreneur’s expertise can sap resources. For instance, trying to develop a killer website or manage an advanced database with no previous experience.
  • Refusing to spend money: Seeking help can be pricey, but avoiding a necessary expense can be disastrous in other ways. “Studies have shown you increase a project’s failure rate when you wait too long to do it,” says Lam. She advises clients to jump on serious issues, bite the monetary bullet and understand that upfront dollars can often prevent future bills.

Entrepreneurs should have a clear understanding of the processes that drive marketing, sales, onboarding, service delivery, and offboarding. This includes examining how each process operates, the reasoning behind their initial selection, and the specific steps each one follows.

Of course, spending that money wisely is the key. To accomplish that, Lam suggests that business owners devote the time and effort to understanding their current issues before trying to adopt potential solutions. “Be honest with yourself,” suggests Lam.

“That clarity helps us plan where we should focus, how to create a new offer or whether to move in another direction.” To do that, they must:

  • Clarify priorities: An honest, upfront assessment of business goals can prevent serious missteps later. Being clear about whether your most important priority is to control working hours, introduce new product lines, deepen existing client relationships, or build a professional reputation as a thought leader can inform the ideal kind of scaling solution to implement.
  • Dive under the hood: Knowing your existing infrastructure is critical. That means thoroughly understanding current processes, where bottlenecks seem to occur and when things begin to seem impossible.

A broad, general understanding of what already lies “under the hood” helps pinpoint which processes are starting to unravel. Lam’s deep dive into Plouffe’s business prompted a substantial update. “We built a lot of automation and revamped the sales and proposal process to make it clear,” says Lam.

Once her new systems were optimized and operating, Plouffe could share earlier-stage design iterations throughout the sales and production process. Clients weren’t left guessing about her design direction. They could see it at any stage and give ongoing feedback. That made them feel seen, included and informed.

Lam even set up automated testimonial capture and referral benefits for clients who brought new business to Plouffe. The branding expert now felt confident she could set expectations well before a project’s completion and, even better, control her working hours.

In fact, once the new system was up and running, Plouffe was finally able to take her first-ever vacation as a digital entrepreneur.

“I’ve gotten back time to take breaks and just live my life without worrying that my business will crumble if I go away,” she says, “and that was something I could only dream up before Diane.”

Being able to understand her software, link her technology to clear business needs, adjust projects to deliver personalized information and follow-up with clients in a painless way turned out to be the ultimate prescription for an entrepreneur’s growing pains.

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Headshot of Susan Treiman
Sue Treiman

Susan Treiman has written for every New York City daily newspaper, countless digital sites, leading international consulting firms and major consumer health publications. As a media professional, she produced ABC's "Good Morning America," was a director at "Entertainment Tonight," earned Emmys at WBBM-TV Chicago and was an Executive Producer for ABC.com.